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Organic Chemistry and Instrumental Analysis
Organic Chemistry and Instrumental Analysis is the second unit within the Advanced Higher Chemistry course. It consists of six subtopics; Molecular orbitals, Molecular structure, Stereo chemistry, Synthesis, Experimental determination of structure and Pharmaceutical chemistry. Subtopics Molecular orbitals * Formation of bonding molecular orbitals. * Hybridisation sp3, sp2 hybrid orbitals and their role in the formation of sigma and pi bonds. * The symmetry and position of bonding orbitals between atoms determines types of bonding Ionic, polar and non-polar covalent bonding. * Absorption of visible light by organic molecules. * An explanation of why organic compounds are colourless or coloured with reference to molecular orbital theory including HOMO and LUMO or conjugated systems. * Describe a Chromophore and explain its role in the colour exhibited by the compound. Molecular structure * Draw and convert between molecular, structural and skeletal formulae with no more than 10 carbon atoms in their longest chain. Stereo chemistry * Stereoisomerism * Geometric isomerism. * cis and trans. Physical and chemical properties of geometric isomers * Optical isomerism. * Non-superimposable mirror image, chiral/enantiomers. Racemic mixture and effect on polarised light. * Physical and chemical properties of optical isomers. Synthesis * From given equations identify: substitution, addition, elimination, condensation, hydrolysis, oxidation, reduction reactions. * Devise synthetic routes, with no more than three steps, from a given reactant to a final product. * Deduce possible reactions from molecular structures. * Homolytic and heterolytic fission. * Electrophiles and Nucleophiles. * Reactions involving heterolytic bond fission. Nucleophiles or electrophiles as attacking groups. * Use of double-headed, single-headed and curly arrows to show electron movement. * Haloalkanes * Classification of monohaloalkanes as primary, secondary or tertiary. * Monohaloalkanes undergo nucleophilic substitution reactions: *# alkalis to form alcohols *# alcoholic alkoxides to form ethers *# ethanolic cyanide to form nitriles which can be hydrolysed to carboxylic acids * Monohaloalkanes- elimination reactions to form alkenes. * The reaction mechanism for SN1 and SN2 reactions and associated factors. * SN1 and SN2 reactions using curly arrows and mechanisms with particular attention given to the transition state/intermediate. * Alcohols * The preparation properties and reactions of alcohols. * Preparation from alkenes, haloalkanes and reduction of carbonyl compounds using lithium aluminium hydride. * Physical properties related to bonding. * Dehydration, reaction with metals, reactions with carboxylic acids and acid chlorides. * Ethers * Naming and general structure. Boiling point related to bonding. Preparation using haloalkanes with alkoxides. Chemical and physical properties of ethers linked to molecular size and uses. * Alkenes * Preparation: *# dehydration of alcohols *# base-induced elimination of hydrogen halides from monohaloalkanes * Electrophilic addition reactions: *# catalytic addition of hydrogen to form alkanes *# Including mechanisms for addition of halogens to form dihaloalkanes *# addition of hydrogen halides according to Markovnikov’s rule, to form monohaloalkanes *# acid-catalysed addition of water according to Markovnikov’s rule, to form alcohols * Carboxylic acids Preparation by: *# oxidising primary alcohols and aldehydes *# hydrolysing nitriles, esters, amides * Reactions: *# formation of salts by reactions with metals or bases *# condensation reactions with alcohols to form esters in the presence of an acid catalyst *# reaction with amino groups to form amide links *# reduction with lithium aluminium hydride to form primary alcohols * Amine * Classification as primary, secondary or tertiary. * Physical properties related to structure. * Amines as weak bases and their use in salt formation. * Aromatic hydrocarbons * Aromatic hydrocarbons and reactions of benzene. * Structure, bonding and stability of the benzene ring. Substitution reactions of benzene (phenyl); alkylation, nitration, sulfonation and halogenation as examples of electrophilic substitution in benzene and other aromatic compounds. Experimental determination of structure * Elemental microanalysis * Determination of the masses of C, H, O, S and N in a sample of an organic compound in order to determine its empirical formula. * Mass spectrometry * Interpretation of fragmentation data from mass spectra to gain structural information. * Infra-red spectroscopy * Interpretation of spectral data from IR to gain structural information. * 1H NMR * Interpretation of 1H NMR spectra. * Interpretation of spectral data to gain structural information. * Draw and analyse low resolution proton NMR spectra and to analyse high resolution proton NMR spectra. Pharmaceutical chemistry * Effect of drugs on the body. * Classification of drugs as agonists or as antagonists. * How drugs work. * Identify the types of interaction between drug functional groups and receptor sites. * Recognise the active structural fragments in drug molecules which confer pharmacological activity * % solution by mass, % solution by volume and ppm, calculations.